JP2005518330A5 - - Google Patents
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- JP2005518330A5 JP2005518330A5 JP2002582930A JP2002582930A JP2005518330A5 JP 2005518330 A5 JP2005518330 A5 JP 2005518330A5 JP 2002582930 A JP2002582930 A JP 2002582930A JP 2002582930 A JP2002582930 A JP 2002582930A JP 2005518330 A5 JP2005518330 A5 JP 2005518330A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- cycloalkyl
- dihydro
- piperidinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 184
- -1 phenyloxy Chemical group 0.000 claims 162
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 84
- 150000001875 compounds Chemical class 0.000 claims 84
- 229910052739 hydrogen Inorganic materials 0.000 claims 75
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 65
- 229910052736 halogen Inorganic materials 0.000 claims 65
- 150000002367 halogens Chemical class 0.000 claims 64
- 125000003545 alkoxy group Chemical group 0.000 claims 60
- 239000001257 hydrogen Substances 0.000 claims 59
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 57
- 125000001424 substituent group Chemical group 0.000 claims 52
- 150000002431 hydrogen Chemical class 0.000 claims 46
- 125000001072 heteroaryl group Chemical group 0.000 claims 44
- 125000004093 cyano group Chemical group *C#N 0.000 claims 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 40
- 125000003118 aryl group Chemical group 0.000 claims 39
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 32
- 125000003282 alkyl amino group Chemical group 0.000 claims 28
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 24
- 125000002619 bicyclic group Chemical group 0.000 claims 24
- 125000004043 oxo group Chemical group O=* 0.000 claims 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims 21
- 229910052799 carbon Inorganic materials 0.000 claims 20
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 16
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 16
- 125000002950 monocyclic group Chemical group 0.000 claims 16
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 16
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 7
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 4
- 125000004442 acylamino group Chemical group 0.000 claims 4
- 125000001118 alkylidene group Chemical group 0.000 claims 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 3
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 3
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 3
- LILQJVUJTFIDBY-UHFFFAOYSA-N 1-[4-(cyclooctylmethylamino)cyclohexyl]-3-ethylbenzimidazol-2-one Chemical compound O=C1N(CC)C2=CC=CC=C2N1C(CC1)CCC1NCC1CCCCCCC1 LILQJVUJTFIDBY-UHFFFAOYSA-N 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- NYVMZCZHOYEYOU-UHFFFAOYSA-N 1-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl)-3-ethylbenzimidazol-2-one Chemical compound C1CC2CCCCC2CC1N1C2=CC=CC=C2N(CC)C1=O NYVMZCZHOYEYOU-UHFFFAOYSA-N 0.000 claims 1
- LQMJWHNITHLMNQ-UHFFFAOYSA-N 1-(1-benzyl-3-methylpiperidin-4-yl)-3h-indol-2-one Chemical compound C1CC(N2C3=CC=CC=C3CC2=O)C(C)CN1CC1=CC=CC=C1 LQMJWHNITHLMNQ-UHFFFAOYSA-N 0.000 claims 1
- HVSVAPSADCIRKD-UHFFFAOYSA-N 1-(1-benzylpiperidin-4-yl)-3-ethylideneindol-2-one Chemical compound C12=CC=CC=C2C(=CC)C(=O)N1C(CC1)CCN1CC1=CC=CC=C1 HVSVAPSADCIRKD-UHFFFAOYSA-N 0.000 claims 1
- KEKPRYDDAKAEDT-UHFFFAOYSA-N 1-[1-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl)-3-methylpiperidin-4-yl]-3-ethyl-3h-indol-2-one Chemical compound C12=CC=CC=C2C(CC)C(=O)N1C1C(C)CN(C2CC3CCCCC3CC2)CC1 KEKPRYDDAKAEDT-UHFFFAOYSA-N 0.000 claims 1
- IGCBPFKTRVLSHK-UHFFFAOYSA-N 1-[1-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl)-3-methylpiperidin-4-yl]-3h-indol-2-one Chemical compound C1CC2CCCCC2CC1N1CC(C)C(N2C3=CC=CC=C3CC2=O)CC1 IGCBPFKTRVLSHK-UHFFFAOYSA-N 0.000 claims 1
- GCFAUTUJXLEZQZ-UHFFFAOYSA-N 1-[1-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl)piperidin-4-yl]-3-ethyl-3h-indol-2-one Chemical compound C12=CC=CC=C2C(CC)C(=O)N1C1CCN(C2CC3CCCCC3CC2)CC1 GCFAUTUJXLEZQZ-UHFFFAOYSA-N 0.000 claims 1
- MGIADQYKMHMDKW-UHFFFAOYSA-N 1-[1-(1,2,3,4-tetrahydronaphthalen-2-yl)piperidin-4-yl]-3h-indol-2-one Chemical compound C1CC2=CC=CC=C2CC1N(CC1)CCC1N1C2=CC=CC=C2CC1=O MGIADQYKMHMDKW-UHFFFAOYSA-N 0.000 claims 1
- VUUHLRJNVMRQFC-UHFFFAOYSA-N 1-[1-(2,3-dihydro-1h-inden-2-yl)piperidin-4-yl]-3-ethyl-3h-indol-2-one Chemical compound C12=CC=CC=C2C(CC)C(=O)N1C1CCN(C2CC3=CC=CC=C3C2)CC1 VUUHLRJNVMRQFC-UHFFFAOYSA-N 0.000 claims 1
- LINLVGOKXHRSPY-UHFFFAOYSA-N 1-[1-(2,3-dihydro-1h-inden-2-yl)piperidin-4-yl]-3-ethylideneindol-2-one Chemical compound C12=CC=CC=C2C(=CC)C(=O)N1C1CCN(C2CC3=CC=CC=C3C2)CC1 LINLVGOKXHRSPY-UHFFFAOYSA-N 0.000 claims 1
- LXZJSJZYHGABNV-UHFFFAOYSA-N 1-[1-(2,3-dihydro-1h-inden-2-yl)piperidin-4-yl]-3h-indol-2-one Chemical compound C1C2=CC=CC=C2CC1N(CC1)CCC1N1C2=CC=CC=C2CC1=O LXZJSJZYHGABNV-UHFFFAOYSA-N 0.000 claims 1
- NWRGLIDLRXTJSD-UHFFFAOYSA-N 1-[1-(3,3-diphenylpropyl)-3-methylpiperidin-4-yl]-3-ethyl-3h-indol-2-one Chemical compound C12=CC=CC=C2C(CC)C(=O)N1C(C(C1)C)CCN1CCC(C=1C=CC=CC=1)C1=CC=CC=C1 NWRGLIDLRXTJSD-UHFFFAOYSA-N 0.000 claims 1
- DLYVRZLQLQGFEN-UHFFFAOYSA-N 1-[1-(3,3-diphenylpropyl)-3-methylpiperidin-4-yl]-3h-indol-2-one Chemical compound C1CC(N2C3=CC=CC=C3CC2=O)C(C)CN1CCC(C=1C=CC=CC=1)C1=CC=CC=C1 DLYVRZLQLQGFEN-UHFFFAOYSA-N 0.000 claims 1
- UVPYEOSMQKEYFY-UHFFFAOYSA-N 1-[1-(3,3-diphenylpropyl)piperidin-4-yl]-3-ethylideneindol-2-one Chemical compound C12=CC=CC=C2C(=CC)C(=O)N1C(CC1)CCN1CCC(C=1C=CC=CC=1)C1=CC=CC=C1 UVPYEOSMQKEYFY-UHFFFAOYSA-N 0.000 claims 1
- FYPZKVTXDSIOLG-UHFFFAOYSA-N 1-[1-(3,3-diphenylpropyl)piperidin-4-yl]-3h-indol-2-one Chemical compound O=C1CC2=CC=CC=C2N1C(CC1)CCN1CCC(C=1C=CC=CC=1)C1=CC=CC=C1 FYPZKVTXDSIOLG-UHFFFAOYSA-N 0.000 claims 1
- KUPBDFJAIIJODB-UHFFFAOYSA-N 1-[1-(3-bicyclo[2.2.1]heptanyl)piperidin-4-yl]-3-ethyl-3h-indol-2-one Chemical compound C12=CC=CC=C2C(CC)C(=O)N1C1CCN(C2C3CCC(C3)C2)CC1 KUPBDFJAIIJODB-UHFFFAOYSA-N 0.000 claims 1
- KXABEEPGAKHMPP-UHFFFAOYSA-N 1-[1-(3-bicyclo[2.2.1]heptanyl)piperidin-4-yl]-3-ethylideneindol-2-one Chemical compound C12=CC=CC=C2C(=CC)C(=O)N1C1CCN(C2C3CCC(C3)C2)CC1 KXABEEPGAKHMPP-UHFFFAOYSA-N 0.000 claims 1
- XZNQOCYOECGHKR-UHFFFAOYSA-N 1-[1-(3-bicyclo[2.2.1]heptanyl)piperidin-4-yl]-3h-indol-2-one Chemical compound O=C1CC2=CC=CC=C2N1C(CC1)CCN1C1C(C2)CCC2C1 XZNQOCYOECGHKR-UHFFFAOYSA-N 0.000 claims 1
- NJRSRMBYKJLFSR-UHFFFAOYSA-N 1-[1-(5-methylhexan-2-yl)piperidin-4-yl]-3h-indol-2-one Chemical compound C1CN(C(C)CCC(C)C)CCC1N1C2=CC=CC=C2CC1=O NJRSRMBYKJLFSR-UHFFFAOYSA-N 0.000 claims 1
- OUYGWBQPUSQZFK-UHFFFAOYSA-N 1-[1-(cyclooctylmethyl)-3-methylpiperidin-4-yl]-3h-indol-2-one Chemical compound C1CC(N2C3=CC=CC=C3CC2=O)C(C)CN1CC1CCCCCCC1 OUYGWBQPUSQZFK-UHFFFAOYSA-N 0.000 claims 1
- XLRVRCJVURLQLB-UHFFFAOYSA-N 1-[1-(cyclooctylmethyl)piperidin-4-yl]-3-ethyl-3h-indol-2-one Chemical compound C12=CC=CC=C2C(CC)C(=O)N1C(CC1)CCN1CC1CCCCCCC1 XLRVRCJVURLQLB-UHFFFAOYSA-N 0.000 claims 1
- OVQQQOSKVXWEGY-UHFFFAOYSA-N 1-[1-(cyclooctylmethyl)piperidin-4-yl]-3-ethylideneindol-2-one Chemical compound C12=CC=CC=C2C(=CC)C(=O)N1C(CC1)CCN1CC1CCCCCCC1 OVQQQOSKVXWEGY-UHFFFAOYSA-N 0.000 claims 1
- QAWBKQCFIWTTBQ-UHFFFAOYSA-N 1-[1-(cyclooctylmethyl)piperidin-4-yl]-3h-indol-2-one Chemical compound O=C1CC2=CC=CC=C2N1C(CC1)CCN1CC1CCCCCCC1 QAWBKQCFIWTTBQ-UHFFFAOYSA-N 0.000 claims 1
- LTWVTPVZLGXHMI-UHFFFAOYSA-N 1-[1-(naphthalen-1-ylmethyl)piperidin-4-yl]-3h-indol-2-one Chemical compound C1=CC=C2C(CN3CCC(CC3)N3C4=CC=CC=C4CC3=O)=CC=CC2=C1 LTWVTPVZLGXHMI-UHFFFAOYSA-N 0.000 claims 1
- ZDTVVSZPPORAQV-UHFFFAOYSA-N 1-[1-(naphthalen-2-ylmethyl)piperidin-4-yl]-3h-indol-2-one Chemical compound C1=CC=CC2=CC(CN3CCC(CC3)N3C4=CC=CC=C4CC3=O)=CC=C21 ZDTVVSZPPORAQV-UHFFFAOYSA-N 0.000 claims 1
- KPTFMFIHJMRPTM-UHFFFAOYSA-N 1-[1-[(4-phenylmethoxyphenyl)methyl]piperidin-4-yl]-3h-indol-2-one Chemical compound O=C1CC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1OCC1=CC=CC=C1 KPTFMFIHJMRPTM-UHFFFAOYSA-N 0.000 claims 1
- BRBIKOPPKYMIJR-UHFFFAOYSA-N 1-[1-[(4-phenylphenyl)methyl]piperidin-4-yl]-3h-indol-2-one Chemical compound O=C1CC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1C1=CC=CC=C1 BRBIKOPPKYMIJR-UHFFFAOYSA-N 0.000 claims 1
- DXPPDNQYXUVLDF-UHFFFAOYSA-N 1-[3-methyl-1-(4-propan-2-ylcyclohexyl)piperidin-4-yl]-3h-indol-2-one Chemical compound C1CC(C(C)C)CCC1N1CC(C)C(N2C3=CC=CC=C3CC2=O)CC1 DXPPDNQYXUVLDF-UHFFFAOYSA-N 0.000 claims 1
- ICQXAZSNLVCTLF-UHFFFAOYSA-N 1-[3-methyl-1-(4-propylcyclohexyl)piperidin-4-yl]-3h-indol-2-one Chemical compound C1CC(CCC)CCC1N1CC(C)C(N2C3=CC=CC=C3CC2=O)CC1 ICQXAZSNLVCTLF-UHFFFAOYSA-N 0.000 claims 1
- GJINFLWSMJVTAH-UHFFFAOYSA-N 1-[3-methyl-1-(5-methylhexan-2-yl)piperidin-4-yl]-3h-indol-2-one Chemical compound CC1CN(C(C)CCC(C)C)CCC1N1C2=CC=CC=C2CC1=O GJINFLWSMJVTAH-UHFFFAOYSA-N 0.000 claims 1
- FMCFTRWLTULAKX-UHFFFAOYSA-N 1-[4-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-ylamino)cyclohexyl]-2-oxo-3h-benzimidazole-5-carboxamide Chemical compound C1CC2CCCCC2CC1NC(CC1)CCC1N1C2=CC=C(C(=O)N)C=C2NC1=O FMCFTRWLTULAKX-UHFFFAOYSA-N 0.000 claims 1
- BDWZSPNHKYJSMH-UHFFFAOYSA-N 1-[4-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-ylamino)cyclohexyl]-3-ethylbenzimidazol-2-one Chemical compound C1CC2CCCCC2CC1NC(CC1)CCC1N1C2=CC=CC=C2N(CC)C1=O BDWZSPNHKYJSMH-UHFFFAOYSA-N 0.000 claims 1
- YDOWFVONEZMYAA-UHFFFAOYSA-N 1-[4-(2,3-dihydro-1h-inden-2-ylamino)cyclohexyl]-2-oxo-3h-benzimidazole-5-carboxamide Chemical compound C1C2=CC=CC=C2CC1NC(CC1)CCC1N1C2=CC=C(C(=O)N)C=C2NC1=O YDOWFVONEZMYAA-UHFFFAOYSA-N 0.000 claims 1
- LUYWJVZXBWBINH-UHFFFAOYSA-N 1-[4-(5-methylhexan-2-ylamino)cyclohexyl]-2-oxo-3h-benzimidazole-5-carboxamide Chemical compound C1CC(NC(C)CCC(C)C)CCC1N1C(=O)NC2=CC(C(N)=O)=CC=C21 LUYWJVZXBWBINH-UHFFFAOYSA-N 0.000 claims 1
- JOQMZORIMNMWNO-UHFFFAOYSA-N 1-[4-(benzylamino)cyclohexyl]-2-oxo-3h-benzimidazole-5-carboxamide Chemical compound O=C1NC2=CC(C(=O)N)=CC=C2N1C(CC1)CCC1NCC1=CC=CC=C1 JOQMZORIMNMWNO-UHFFFAOYSA-N 0.000 claims 1
- TYSMIRKJWOUVRO-UHFFFAOYSA-N 1-[4-(benzylamino)cyclohexyl]-3-ethylbenzimidazol-2-one Chemical compound O=C1N(CC)C2=CC=CC=C2N1C(CC1)CCC1NCC1=CC=CC=C1 TYSMIRKJWOUVRO-UHFFFAOYSA-N 0.000 claims 1
- RDQLCLLGFNYKLN-UHFFFAOYSA-N 1-[4-(cyclooctylamino)cyclohexyl]-2-oxo-3h-benzimidazole-5-carboxamide Chemical compound O=C1NC2=CC(C(=O)N)=CC=C2N1C(CC1)CCC1NC1CCCCCCC1 RDQLCLLGFNYKLN-UHFFFAOYSA-N 0.000 claims 1
- KWOYLCCMQIYFLV-UHFFFAOYSA-N 1-[4-(dibenzylamino)cyclohexyl]-2-oxo-3h-benzimidazole-5-carboxamide Chemical compound O=C1NC2=CC(C(=O)N)=CC=C2N1C(CC1)CCC1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 KWOYLCCMQIYFLV-UHFFFAOYSA-N 0.000 claims 1
- OOUXBZOOFSNPDU-UHFFFAOYSA-N 1-[4-[benzyl(2,3-dihydro-1h-inden-2-yl)amino]cyclohexyl]-3-ethylbenzimidazol-2-one Chemical compound O=C1N(CC)C2=CC=CC=C2N1C(CC1)CCC1N(C1CC2=CC=CC=C2C1)CC1=CC=CC=C1 OOUXBZOOFSNPDU-UHFFFAOYSA-N 0.000 claims 1
- SFGGSFKSBNZWNX-UHFFFAOYSA-N 1-benzyl-3-ethylbenzimidazol-2-one Chemical compound O=C1N(CC)C2=CC=CC=C2N1CC1=CC=CC=C1 SFGGSFKSBNZWNX-UHFFFAOYSA-N 0.000 claims 1
- LDWLKZLPOVQLOH-UHFFFAOYSA-N 1-ethyl-3-(4-propylcyclohexyl)benzimidazol-2-one Chemical compound C1CC(CCC)CCC1N1C(=O)N(CC)C2=CC=CC=C21 LDWLKZLPOVQLOH-UHFFFAOYSA-N 0.000 claims 1
- FCXWYYMEXWVASJ-UHFFFAOYSA-N 1-ethyl-3-(5-methylhexan-2-yl)benzimidazol-2-one Chemical compound C1=CC=C2N(C(C)CCC(C)C)C(=O)N(CC)C2=C1 FCXWYYMEXWVASJ-UHFFFAOYSA-N 0.000 claims 1
- NMOONDNEDCFSGW-UHFFFAOYSA-N 1-ethyl-3-(naphthalen-1-ylmethyl)benzimidazol-2-one Chemical compound C1=CC=C2C(CN3C4=CC=CC=C4N(C3=O)CC)=CC=CC2=C1 NMOONDNEDCFSGW-UHFFFAOYSA-N 0.000 claims 1
- QKFZSJPUZHFGHY-UHFFFAOYSA-N 1-ethyl-3-(naphthalen-2-ylmethyl)benzimidazol-2-one Chemical compound C1=CC=CC2=CC(CN3C4=CC=CC=C4N(C3=O)CC)=CC=C21 QKFZSJPUZHFGHY-UHFFFAOYSA-N 0.000 claims 1
- DAODRBATUZJZHS-UHFFFAOYSA-N 1-ethyl-3-[(4-phenylmethoxyphenyl)methyl]benzimidazol-2-one Chemical compound O=C1N(CC)C2=CC=CC=C2N1CC(C=C1)=CC=C1OCC1=CC=CC=C1 DAODRBATUZJZHS-UHFFFAOYSA-N 0.000 claims 1
- GWIYEJNNCJDCCP-UHFFFAOYSA-N 1-ethyl-3-[(4-phenylphenyl)methyl]benzimidazol-2-one Chemical compound O=C1N(CC)C2=CC=CC=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1 GWIYEJNNCJDCCP-UHFFFAOYSA-N 0.000 claims 1
- FLWIPFTXSGPABH-UHFFFAOYSA-N 1-ethyl-3-[4-(naphthalen-2-ylamino)cyclohexyl]benzimidazol-2-one Chemical compound C1=CC=CC2=CC(NC3CCC(CC3)N3C4=CC=CC=C4N(C3=O)CC)=CC=C21 FLWIPFTXSGPABH-UHFFFAOYSA-N 0.000 claims 1
- SUOCZWNUONQVBE-UHFFFAOYSA-N 1-ethyl-3-[4-[(4-phenylmethoxyphenyl)methylamino]cyclohexyl]benzimidazol-2-one Chemical compound O=C1N(CC)C2=CC=CC=C2N1C(CC1)CCC1NCC(C=C1)=CC=C1OCC1=CC=CC=C1 SUOCZWNUONQVBE-UHFFFAOYSA-N 0.000 claims 1
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| US28466601P | 2001-04-18 | 2001-04-18 | |
| US28466701P | 2001-04-18 | 2001-04-18 | |
| US28466901P | 2001-04-18 | 2001-04-18 | |
| US28466801P | 2001-04-18 | 2001-04-18 | |
| PCT/US2002/012351 WO2002085357A1 (en) | 2001-04-18 | 2002-04-18 | Nociceptin analogs |
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| JP2009150368A Division JP5081870B2 (ja) | 2001-04-18 | 2009-06-24 | ノシセプチン類似体 |
| JP2009150370A Division JP2009263380A (ja) | 2001-04-18 | 2009-06-24 | ノシセプチン類似体 |
| JP2009150369A Division JP5189562B2 (ja) | 2001-04-18 | 2009-06-24 | ノシセプチン類似体 |
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| JP4364513B2 JP4364513B2 (ja) | 2009-11-18 |
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| JP2009150369A Expired - Fee Related JP5189562B2 (ja) | 2001-04-18 | 2009-06-24 | ノシセプチン類似体 |
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| JP2009150369A Expired - Fee Related JP5189562B2 (ja) | 2001-04-18 | 2009-06-24 | ノシセプチン類似体 |
| JP2009150368A Expired - Fee Related JP5081870B2 (ja) | 2001-04-18 | 2009-06-24 | ノシセプチン類似体 |
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| US (4) | US6867222B2 (https=) |
| EP (7) | EP1918279A3 (https=) |
| JP (4) | JP4364513B2 (https=) |
| KR (2) | KR100847296B1 (https=) |
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| AT (4) | ATE434607T1 (https=) |
| AU (1) | AU2002307416B2 (https=) |
| BR (1) | BR0209129A (https=) |
| CA (1) | CA2444198C (https=) |
| CL (2) | CL2009001278A1 (https=) |
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| IL (4) | IL158484A0 (https=) |
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| PT (4) | PT1598338E (https=) |
| SI (4) | SI1379246T1 (https=) |
| WO (1) | WO2002085357A1 (https=) |
| YU (1) | YU82303A (https=) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6615189B1 (en) * | 1998-06-22 | 2003-09-02 | Bank One, Delaware, National Association | Debit purchasing of stored value card for use by and/or delivery to others |
| IL158484A0 (en) | 2001-04-18 | 2004-05-12 | Euro Celtique Sa | Nociceptin analogs |
| DE10252665A1 (de) | 2002-11-11 | 2004-06-03 | Grünenthal GmbH | 4-Aminomethyl-1-aryl-cyclohexylamin-Derivate |
| WO2004064835A1 (en) * | 2003-01-17 | 2004-08-05 | Neurosearch A/S | Use of ion channel modulating agents for treating pain |
| WO2004078748A2 (en) | 2003-02-28 | 2004-09-16 | Bayer Pharmaceuticals Corporation | Novel bicyclic urea derivatives useful in the treatment of cancer and other disorders |
| US20050228023A1 (en) * | 2003-12-19 | 2005-10-13 | Sri International | Agonist and antagonist ligands of the nociceptin receptor |
| WO2005075459A1 (en) * | 2004-02-03 | 2005-08-18 | Euro-Celtique S.A. | Synthesis of cyanoimino-benzoimidazoles |
| EP1847530A1 (en) * | 2005-01-31 | 2007-10-24 | Kyowa Hakko Kogyo Co., Ltd. | Diamine derivative |
| ATE429428T1 (de) * | 2005-09-30 | 2009-05-15 | Hoffmann La Roche | Indanderivate als antagonisten des mch-rezeptors |
| WO2007084728A2 (en) * | 2006-01-19 | 2007-07-26 | Abbott Laboratories | 2-imino-benzimidazoles |
| JP2009525269A (ja) * | 2006-01-30 | 2009-07-09 | ユーロ−セルティーク エス．エイ． | カルシウムチャネルブロッカーとしての環状尿素化合物 |
| TW200813018A (en) | 2006-06-09 | 2008-03-16 | Astrazeneca Ab | Novel compounds |
| US20080051380A1 (en) | 2006-08-25 | 2008-02-28 | Auerbach Alan H | Methods and compositions for treating cancer |
| US20080287479A1 (en) * | 2006-12-20 | 2008-11-20 | Pfizer Inc | Inhibitors of serine palmitoyltransferase |
| EP2397477B1 (en) * | 2007-01-16 | 2014-03-05 | Purdue Pharma LP | Heterocyclic-substituted piperidine compounds and the uses thereof |
| BRPI0808025A2 (pt) * | 2007-03-01 | 2014-06-24 | Mitsubishi Tanabe Pharma Corp | Composto de benzimidazol e uso farmacêutico do mesmo |
| MY150602A (en) * | 2007-08-31 | 2014-01-30 | Purdue Pharma Lp | Subtituted-quinoxaline-type piperidine compounds and the uses thereof |
| US8119661B2 (en) | 2007-09-11 | 2012-02-21 | Astrazeneca Ab | Piperidine derivatives and their use as muscarinic receptor modulators |
| EP2185181A2 (en) * | 2007-09-11 | 2010-05-19 | Mondobiotech Laboratories AG | Therapeutic uses of gastrin-1 and g-pen-grgdspca |
| US8697722B2 (en) | 2007-11-02 | 2014-04-15 | Sri International | Nicotinic acetylcholine receptor modulators |
| KR101333660B1 (ko) | 2008-07-21 | 2013-11-27 | 시오노기세이야쿠가부시키가이샤 | 치환-퀴녹살린-형 가교-피페리딘 화합물 및 그의 용도 |
| GB0817982D0 (en) * | 2008-10-01 | 2008-11-05 | Glaxo Group Ltd | Compounds |
| RU2560729C2 (ru) | 2010-01-11 | 2015-08-20 | АСТРАЕА ТЕРАПЕУТИКС, ЭлЭлСи | Модуляторы никотиновых ацетилхолиновых рецепторов |
| IN2014CN02959A (https=) | 2011-10-28 | 2015-07-03 | Merck Sharp & Dohme | |
| TW201348231A (zh) * | 2012-02-29 | 2013-12-01 | Amgen Inc | 雜雙環化合物 |
| WO2014102588A2 (en) | 2012-12-27 | 2014-07-03 | Purdue Pharma L.P. | Indole and indoline-type piperidine compounds and uses thereof |
| US10118927B2 (en) | 2012-12-27 | 2018-11-06 | Purdue Pharma L.P. | Substituted piperidin-4-amino-type compounds and uses thereof |
| WO2014102594A2 (en) | 2012-12-27 | 2014-07-03 | Purdue Pharma L.P. | Substituted benzimidazole-type piperidine compounds and uses thereof |
| US9951038B2 (en) | 2012-12-27 | 2018-04-24 | Purdue Pharma L.P. | Quinazolin-4(3H)-one-type piperidine compounds and uses thereof |
| WO2014106238A1 (en) | 2012-12-31 | 2014-07-03 | Fang, Qun, Kevin | Heterocyclic compounds and methods of use thereof |
| US10112924B2 (en) * | 2015-12-02 | 2018-10-30 | Astraea Therapeutics, Inc. | Piperdinyl nociceptin receptor compounds |
| CN108883103A (zh) * | 2015-12-02 | 2018-11-23 | 阿斯特来亚治疗有限责任公司 | 哌啶基痛敏肽受体化合物 |
| UA124972C2 (uk) | 2016-07-29 | 2021-12-22 | Янссен Фармацевтика Нв | Способи лікування раку передміхурової залози |
Family Cites Families (78)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US49212A (en) * | 1865-08-08 | Improvement in submerged force-pumps | ||
| US171360A (en) * | 1875-12-21 | Improvement in mortising-machines | ||
| US3161645A (en) | 1962-12-18 | 1964-12-15 | Res Lab Dr C Janssen N V | 1-(1-aroylpropyl-4-piperidyl)-2-benzimidazolinones and related compounds |
| US3318900A (en) | 1964-05-06 | 1967-05-09 | Janssen Pharmaceutica Nv | Derivatives of benzimidazolinyl piperidine |
| US3325499A (en) * | 1964-11-02 | 1967-06-13 | Mcneilab Inc | 1-(1-hydrocarbyl-4-piperdyl)-2-indolinone |
| US3325490A (en) * | 1965-02-23 | 1967-06-13 | Rexall Drug Chemical | Substituted 1-hydroxydibenzopyrans |
| DE2609645A1 (de) * | 1976-03-09 | 1977-09-15 | Boehringer Sohn Ingelheim | Aminoalkylheterocyclen |
| EP0029707B1 (en) * | 1979-11-21 | 1984-02-01 | Kyowa Hakko Kogyo Co., Ltd | Novel piperidine derivatives, method for the preparation thereof and pharmaceutical compositions containing them |
| US4329353A (en) | 1980-10-22 | 1982-05-11 | Janssen Pharmaceutica, N.V. | 1-(4-Aryl-cyclohexyl)piperidine derivatives, method of use thereof and pharmaceutical compositions thereof |
| US4410528A (en) * | 1980-05-16 | 1983-10-18 | Kyowa Hakko Kogyo Co., Ltd. | Hypotensive piperidine derivatives |
| JPS58180481A (ja) | 1982-04-15 | 1983-10-21 | Kyowa Hakko Kogyo Co Ltd | 新規なピペリジン誘導体 |
| JPS60120872A (ja) | 1983-12-01 | 1985-06-28 | Kyowa Hakko Kogyo Co Ltd | 新規なヘテロ環状化合物及び強心剤 |
| DE3827641A1 (de) * | 1988-08-16 | 1990-03-08 | Basf Ag | 2,6-polyalkylpiperidinsubstituierte bislactame und deren verwendung zum stabilisieren von organischem material, insbesondere von kunststoffen und damit stabilisiertes material |
| DE4332168A1 (de) | 1993-02-22 | 1995-03-23 | Thomae Gmbh Dr K | Cyclische Derivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| EP0714299B1 (en) * | 1993-07-16 | 2002-04-24 | Merck & Co. Inc. | Benzoxazinone and benzopyrimidinone piperidinyl tocolytic oxytocin receptor antagonists |
| FR2708608B1 (fr) * | 1993-07-30 | 1995-10-27 | Sanofi Sa | Dérivés de N-sulfonylbenzimidazolone, leur préparation, les compositions pharmaceutiques en contenant. |
| GB9325074D0 (en) | 1993-12-07 | 1994-02-02 | Zeneca Ltd | Bicyclic heterocycles |
| CA2187767A1 (en) * | 1994-04-14 | 1995-10-26 | Joel R. Huff | Alpha1c adrenergic receptor antagonists |
| FR2722190B1 (fr) * | 1994-07-05 | 1996-10-04 | Sanofi Sa | Derives de 1-benzyl-1,3-dihydro-2h-benzimidazol-2-one, leur preparation, les compositions pharmaceutique en contenant |
| WO1996005166A1 (en) * | 1994-08-11 | 1996-02-22 | Yamanouchi Pharmaceutical Co., Ltd. | Substituted amine derivative and medicinal composition containing the same |
| US5767118A (en) * | 1994-10-26 | 1998-06-16 | Merck & Co., Inc. | 4-Heterocyclic peperidines promote release of growth hormone |
| JP2002515008A (ja) * | 1994-10-27 | 2002-05-21 | メルク エンド カンパニー インコーポレーテッド | ムスカリン・アンタゴニスト |
| US5574044A (en) * | 1994-10-27 | 1996-11-12 | Merck & Co., Inc. | Muscarine antagonists |
| US5576321A (en) * | 1995-01-17 | 1996-11-19 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| US5789402A (en) * | 1995-01-17 | 1998-08-04 | Eli Lilly Company | Compounds having effects on serotonin-related systems |
| GB9603457D0 (https=) * | 1996-02-19 | 1996-04-17 | Merck & Co Inc | |
| HRP960159A2 (en) * | 1995-04-21 | 1997-08-31 | Bayer Ag | Benzocyclopentane oxazolidinones containing heteroatoms |
| ES2247604T3 (es) | 1995-06-12 | 2006-03-01 | G.D. SEARLE & CO. | Composiciones que comprenden un inhibidor de ciclooxigenasa-2 y un inhibidor de 5-lipoxigenasa. |
| EP0974583B1 (en) | 1995-09-13 | 2002-05-29 | Kyowa Hakko Kogyo Co., Ltd. | Phenylpiperidine derivatives |
| ZA9610745B (en) * | 1995-12-22 | 1997-06-24 | Warner Lambert Co | 4-Subsituted piperidine analogs and their use as subtype selective nmda receptor antagonists |
| EP0891359A1 (de) * | 1996-03-30 | 1999-01-20 | Roche Diagnostics GmbH | Neue oxazolidinderivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| US5891889A (en) * | 1996-04-03 | 1999-04-06 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| EP0944388A4 (en) * | 1996-04-03 | 2001-08-16 | Merck & Co Inc | INHIBITORS OF FARNESYL PROTEIN TRANSFERASE |
| US6180649B1 (en) | 1996-04-19 | 2001-01-30 | Nerosearch A/S | 1-(4-piperidyl)-benzimidazoles having neurotrophic activity |
| SK285631B6 (sk) * | 1996-09-10 | 2007-05-03 | Dr. Karl Thomae Gmbh | Modifikované aminokyseliny, farmaceutický prostriedok s ich obsahom a ich použitie |
| US5977134A (en) | 1996-12-05 | 1999-11-02 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US6300325B1 (en) | 1997-01-23 | 2001-10-09 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6117973A (en) | 1997-02-24 | 2000-09-12 | Georgia Tech Research Corp. | PNA monomers with electron donor or acceptor |
| TWI242011B (en) * | 1997-03-31 | 2005-10-21 | Eisai Co Ltd | 1,4-substituted cyclic amine derivatives |
| US6063796A (en) * | 1997-04-04 | 2000-05-16 | Merck & Co., Inc. | Somatostatin agonists |
| ES2226129T3 (es) | 1997-05-30 | 2005-03-16 | Banyu Pharmaceutical Co., Ltd. | Derivados de 2-0x0imidazol. |
| JPH10330377A (ja) * | 1997-06-02 | 1998-12-15 | Kyowa Hakko Kogyo Co Ltd | ピペリジン誘導体 |
| US6166037A (en) | 1997-08-28 | 2000-12-26 | Merck & Co., Inc. | Pyrrolidine and piperidine modulators of chemokine receptor activity |
| EP1009405A4 (en) * | 1997-08-28 | 2001-05-09 | Merck & Co Inc | PAYRROLIDINE AND PIPERIDINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY |
| SI0921125T1 (en) | 1997-12-05 | 2002-04-30 | F. Hoffmann-La Roche Ag | 1,3,8-Triazaspiro(4,5)decan-4-on derivatives |
| US6166209A (en) | 1997-12-11 | 2000-12-26 | Hoffmann-La Roche Inc. | Piperidine derivatives |
| AU2307999A (en) * | 1997-12-23 | 1999-07-12 | Alcon Laboratories, Inc. | Muscarinic agents and use thereof to treat glaucoma, myopia and various other conditions |
| AU1679099A (en) * | 1998-01-19 | 1999-08-02 | Pfizer Inc. | 4-(2-keto-1-benzimidazolinyl)piperidine compounds as orl1-receptor agonists |
| TR200002182T2 (tr) | 1998-01-27 | 2000-12-21 | Aventis Pharmaceuticals Products Inc. | İkame edilmiş aksozaherosayklil faktör xa inhibitörleri |
| NZ507760A (en) | 1998-03-26 | 2002-10-25 | Japan Tobacco Inc | Amide derivatives and nociceptin antagonists |
| AU3809999A (en) | 1998-05-18 | 1999-12-06 | Novo Nordisk A/S | Novel 1,3,8-triazaspiro[4.5]decanones with high affinity for opioid receptor subtypes |
| ID29137A (id) * | 1998-07-27 | 2001-08-02 | Schering Corp | Ligan-ligan afinitas tinggi untuk reseptor nosiseptin orl-1 |
| US6262066B1 (en) | 1998-07-27 | 2001-07-17 | Schering Corporation | High affinity ligands for nociceptin receptor ORL-1 |
| MA26659A1 (fr) * | 1998-08-06 | 2004-12-20 | Pfizer | Dérivés de benzimidazole nouveaux, compositions pharmaceutiques les contenant et procédé pour leur préparation. |
| JP2002524399A (ja) | 1998-09-09 | 2002-08-06 | 石原産業株式会社 | 除草剤として有用な縮合ベンゼン誘導体 |
| CA2355886C (en) | 1998-12-23 | 2006-10-31 | Schering Corporation | Substituted oximes and hydrazones as neurokinin antagonists |
| US6204265B1 (en) | 1998-12-23 | 2001-03-20 | Schering Corporation | Substituted oximes and hydrazones as neurokinin antagonists |
| WO2000038720A1 (en) * | 1998-12-24 | 2000-07-06 | Meiji Seika Kaisha, Ltd. | Remedies for pain |
| JP4011819B2 (ja) * | 1999-04-12 | 2007-11-21 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | インドール誘導体の製造法およびその中間体 |
| AU5567000A (en) | 1999-06-24 | 2001-01-09 | Toray Industries, Inc. | Alpha1b-adrenergic receptor antagonists |
| US6340681B1 (en) | 1999-07-16 | 2002-01-22 | Pfizer Inc | 2-benzimidazolylamine compounds as ORL-1-receptor agonists |
| IL147309A0 (en) * | 1999-07-21 | 2002-08-14 | Fujisawa Pharmaceutical Co | Benzimidazolone derivatives and pharmaceutical compositions containg the same |
| AU1816901A (en) * | 1999-12-06 | 2001-06-12 | Euro-Celtique S.A. | Benzimidazole compounds having nociceptin receptor affinity |
| SE9904652D0 (sv) | 1999-12-17 | 1999-12-17 | Astra Pharma Prod | Novel Compounds |
| EP1122257B1 (en) | 2000-01-05 | 2005-10-12 | Pfizer Inc. | Benzimidazole compounds as ORL1-receptor agonists |
| US6916822B2 (en) * | 2000-02-18 | 2005-07-12 | Meiji Seika Kaisha, Ltd. | Phenoxyalkylamine derivatives useful as opioid δ receptor agonists |
| AU2001238690A1 (en) * | 2000-03-14 | 2001-09-24 | Sepracor, Inc. | 3-substituted piperidines comprising urea functionality, and methods of use thereof |
| CA2404280A1 (en) * | 2000-03-24 | 2002-09-23 | Meiji Seika Kaisha, Ltd. | Diphenylalkylamine derivatives useful as opioid .delta. receptor agonists |
| EP1285909B1 (en) | 2000-05-29 | 2008-08-20 | Chugai Seiyaku Kabushiki Kaisha | Process for the production of nitrogen compounds |
| EP1167969A2 (en) | 2000-06-14 | 2002-01-02 | Pfizer Inc. | Method and system for predicting pharmacokinetic properties |
| EP1309593B1 (en) * | 2000-08-14 | 2006-03-15 | Ortho-McNeil Pharmaceutical, Inc. | Substituted pyrazoles |
| JP2004531456A (ja) * | 2000-09-06 | 2004-10-14 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | 置換ピラゾールを用いてアレルギーを治療する方法 |
| US20040267010A1 (en) * | 2001-02-02 | 2004-12-30 | Forbes Ian Thomson | Sulfonamide compounds, their preparation and use |
| AR035230A1 (es) * | 2001-03-19 | 2004-05-05 | Astrazeneca Ab | Compuestos de bencimidazol, proceso para su preparacion, composicion farmaceutica, proceso para la preparacion de dicha composicion farmaceutica, y usos de estos compuestos para la elaboracion de medicamentos |
| IL158484A0 (en) * | 2001-04-18 | 2004-05-12 | Euro Celtique Sa | Nociceptin analogs |
| NZ528820A (en) | 2001-04-19 | 2007-01-26 | Eisai Co Ltd | 2-iminopyrrolidine derivatives |
| EA006708B1 (ru) | 2001-10-22 | 2006-02-24 | Пфайзер Продактс Инк. | Производные 3-азабицикло (3.1.0) гексана в качестве антагонистов опиоидного рецептора |
| CA2465328C (en) | 2001-11-01 | 2011-06-14 | Michael Francis Gross | Piperidines |
-
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- 2002-04-18 EP EP05014115A patent/EP1598338B9/en not_active Expired - Lifetime
- 2002-04-18 SI SI200230811T patent/SI1598338T1/sl unknown
- 2002-04-18 BR BR0209129-1A patent/BR0209129A/pt not_active IP Right Cessation
- 2002-04-18 DK DK05014116T patent/DK1598339T3/da active
- 2002-04-18 DK DK05014115.9T patent/DK1598338T5/da active
- 2002-04-18 PT PT05014117T patent/PT1598340E/pt unknown
-
2003
- 2003-10-17 NO NO20034661A patent/NO20034661L/no not_active Application Discontinuation
- 2003-10-19 IL IL158484A patent/IL158484A/en not_active IP Right Cessation
-
2005
- 2005-01-11 US US11/032,955 patent/US7495109B2/en not_active Expired - Fee Related
-
2009
- 2009-01-08 CY CY20091100010T patent/CY1108707T1/el unknown
- 2009-02-23 US US12/390,683 patent/US7939670B2/en not_active Expired - Lifetime
- 2009-04-29 CY CY20091100475T patent/CY1109053T1/el unknown
- 2009-05-22 CY CY20091100552T patent/CY1109092T1/el unknown
- 2009-05-25 CL CL2009001278A patent/CL2009001278A1/es unknown
- 2009-05-25 CL CL2009001279A patent/CL2009001279A1/es unknown
- 2009-06-24 JP JP2009150370A patent/JP2009263380A/ja active Pending
- 2009-06-24 JP JP2009150369A patent/JP5189562B2/ja not_active Expired - Fee Related
- 2009-06-24 JP JP2009150368A patent/JP5081870B2/ja not_active Expired - Fee Related
- 2009-09-10 CY CY20091100940T patent/CY1109352T1/el unknown
-
2010
- 2010-10-24 IL IL208903A patent/IL208903A/en not_active IP Right Cessation
- 2010-10-24 IL IL208907A patent/IL208907A/en not_active IP Right Cessation
-
2011
- 2011-03-18 US US13/051,629 patent/US8252815B2/en not_active Expired - Fee Related
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